Cas no 90-34-6 (Primaquine)

Primaquine structure
Primaquine structure
Product Name:Primaquine
CAS No:90-34-6
MF:C15H21N3O
MW:259.346743345261
MDL:MFCD00598906
CID:34560
PubChem ID:4908
Update Time:2024-10-26

Primaquine Chemical and Physical Properties

Names and Identifiers

    • 8-(4-Amino-1-methylbutylamino)-6-methoxyquinoline
    • N-(6-Methoxyquinolin-8-yl)pentane-1,4-diamine
    • 4-N-(6-methoxyquinolin-8-yl)pentane-1,4-diamine
    • Primaquine
    • Primaquine phosphate
    • [14C]-Primaquine
    • N'-(6-methoxy-8-quinolinyl)-1,4-pentanediamine
    • N4-(6-methoxy-8-quinolinyl)1,4-pentanediamine
    • Neo-Quipenyl
    • Primachin
    • Primachinum
    • Primaquin
    • Primaquina
    • Primaquinum
    • N(4)-(6-methoxyquinolin-8-yl)pentane-1,4-diamine
    • C07627
    • BRD-A55913614-316-06-2
    • KBio3_001723
    • STL146416
    • 1,4-Pentanediamine, N4-(6-methoxy-8-quinolinyl)-
    • SN 13,272
    • HMS2090J17
    • primaquin-
    • Maliride; NSC 27296; Neo-Quipenyl; Primachin
    • LS-141312
    • TG1-297
    • SPBio_002551
    • 4-amino-1-methylbutyl(6-methoxy-8-quinolyl)amine
    • EN300-144245
    • Primaquine (INN)
    • HSDB 6516
    • Quinoline, 8-[(4-amino-1-methylbutyl)amino]-6-methoxy-(6CI,8CI)
    • KBio2_003878
    • 1,4-Pentanediamine, N4-(6-methoxy-8-quinolinyl)-, phosphate(1:2)
    • Primachina
    • cid_359247
    • (-)-Primaquine
    • EINECS 201-987-2
    • WR-2975
    • Spectrum_000830
    • N4-(6-Methoxyquinolin-8-yl)pentane-1,4-diamine (2 H3PO4)
    • N4-(6-methoxyquinolin-8-yl)pentane-1,4-diamine
    • BRN 0019337
    • KBio2_001310
    • NCI60_005887
    • PRIMAQUINE [MI]
    • 57152-47-3
    • AKOS005721199
    • (-)-N4-(6-Methoxy-8-quinolinyl)-1,4-pentanediamine
    • DTXSID8023509
    • Prestwick3_000476
    • 1,4-Pentanediamine, N(4)-(6-methoxy-8-quinolinyl)-
    • Quinoline, 8-[(4-amino-1-methylbutyl)amino]-6-methoxy-
    • AS-30679
    • NCGC00178754-06
    • NSC27296
    • KBio1_000806
    • 4-N-(6-methoxyquinolin-8-yl)pentane-1,4-diamine;phosphoric acid
    • DB01087
    • Quinoline, 8-(4-amino-1-methylbutylamino)-6-methoxy
    • primaquinbis(phosphat)
    • 4-22-00-05817 (Beilstein Handbook Reference)
    • (+)-Primaquine
    • MVR3634GX1
    • Quinoline, 8-((4-amino-1-methylbutyl)amino)-6-methoxy-
    • n4-[6-methoxy-8-quinolinyl]-1,4-pentanediamine
    • Epitope ID:131792
    • AC-23007
    • AB00053529_12
    • N~4~-(6-methoxyquinolin-8-yl)pentane-1,4-diamine
    • C15-H21-N3-O.2H3-O4-P
    • NCGC00178754-02
    • S. N. 13272
    • PRIMAQUINE [WHO-DD]
    • BCP29271
    • SCHEMBL22207
    • N-(5-aminopentan-2-yl)-6-methoxyquinolin-8-amine
    • N4-(6-methoxyquinolin-8-yl)pentane-1,4-diamine;phosphoric acid
    • HY-12651A
    • Oprea1_546209
    • N4-(6-methoxy-8-quinolyl)pentane-1,4-diamine;Primaquine
    • Primaquinum [INN-Latin]
    • NSC 27296
    • Kanaprim
    • MFCD00598906
    • N-[(S)-4-Amino-1-methylbutyl]-6-methoxy-8-quinolinamine
    • UNII-MVR3634GX1
    • SN-13272
    • KBioSS_001310
    • TG1-296
    • BDBM71542
    • 1, N4-(6-methoxy-8-quinolinyl)-
    • GTPL9952
    • A843518
    • Maliride
    • D0T1LK
    • CS-0013754
    • 8-((4-Amino-1-methylbutyl)amino)-6-methoxyquinoline
    • Spectrum3_000552
    • PRIMAQUINE [INN]
    • SBI-0051491.P003
    • N4-(6-Methoxy-8-quinolinyl)-1,4-pentanediamine
    • Spectrum5_001363
    • 8-(4-Amino-1-m
    • KBioGR_000967
    • (+)-N4-(6-Methoxy-8-quinolinyl)-1,4-pentanediamine
    • CCRIS 4109
    • DRG-0026
    • NCGC00178754-01
    • 6-Methoxy-8-[(4-amino-1-methylbutyl)amino]quinoline
    • CHEBI:8405
    • 6-Methoxy-8-((4-amino-1-methylbutyl)amino)quinoline
    • C15H21N3O
    • AB00053529-11
    • D08420
    • (+/-)-Primaquine
    • Spectrum2_000887
    • FT-0687514
    • 1,4-Pentanediamine, N4-(6-methoxy-8-quinolinyl)-(9CI)
    • Primaquine Bis-Phosphoric Acid
    • Prestwick2_000476
    • ethylbutylamino)-6-methoxyquinoline
    • Kanaprim (TN)
    • AB00053529_14
    • SR-05000001864-11
    • Quinoline, 8-(4-amino-1-methylbutylamino)-6-methoxy-
    • Prestwick1_000476
    • (RS)-primaquine
    • NINDS_000806
    • NSC-27296
    • SPBio_000674
    • BBL011330
    • WR 2975
    • N4-(6-methoxy-8-quinolyl)pentane-1,4-diamine
    • SN 13272
    • Prestwick0_000476
    • 6-Methoxy-8-(4-amino-1-methylbutylamino)quinoline
    • Primaquina [INN-Spanish]
    • BSPBio_000612
    • MLS001334045
    • N~4~-[6-(methyloxy)quinolin-8-yl]pentane-1,4-diamine
    • BSPBio_002223
    • NCI60_001035
    • (4-amino-1-methyl-butyl)-(6-methoxy-8-quinolyl)amine;phosphoric acid
    • SMR000875314
    • N4-(6-methoxy-8-quinolinyl)pentane-1,4-diamine;phosphoric acid
    • SMP1_000263
    • PRIMAQUINE [VANDF]
    • dl-Primaquine
    • Q419834
    • DivK1c_000806
    • 90-34-6
    • CHEMBL506
    • Primaquine [INN:BAN]
    • Spectrum4_000484
    • WLN: T66 BNJ HO1 JMY1&3Z
    • IDI1_000806
    • NCGC00178754-03
    • AB00053529
    • 6-Methoxy-8-[4-amino-1-methylbutylamino]quinoline
    • BPBio1_000674
    • Primachina [DCIT]
    • KBio2_006446
    • 8-[(4-Amino-1-methylbutyl)amino]-6-methoxyquinoline
    • 1,4-Pentanediamine, N(4)-(6-methoxy-8-quinolinyl)-, phosphate (1:2)
    • N4-(6-Methoxy-8-quinolinyl)-1,4-pentanediamine (ACI)
    • Quinoline, 8-[(4-amino-1-methylbutyl)amino]-6-methoxy- (6CI, 8CI)
    • (±)-Primaquine
    • 1,4-Pentanediamine N4-(6-methoxy-8-quinolinyl)-
    • Leoprime
    • Malirid
    • MeSH ID: D011319
    • Pimaquin
    • Primacip
    • Primalex
    • DTXCID903509
    • P01BA03
    • NS00000469
    • Primaquina (INN-Spanish)
    • N-(6-Methoxy-8-quinolinyl)-1,4-pentanediamine
    • Primaquinum (INN-Latin)
    • BRD-A55913614-316-09-6
    • BRD-A55913614-316-08-8
    • MDL： MFCD00598906
    • Inchi： 1S/C15H21N3O/c1-11(5-3-7-16)18-14-10-13(19-2)9-12-6-4-8-17-15(12)14/h4,6,8-11,18H,3,5,7,16H2,1-2H3
    • InChI Key： INDBQLZJXZLFIT-UHFFFAOYSA-N
    • SMILES： N1C2C(=CC(=CC=2NC(CCCN)C)OC)C=CC=1

Computed Properties

  • Exact Mass: 259.16800
  • Monoisotopic Mass: 259.168
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 19
  • Rotatable Bond Count: 6
  • Complexity: 262
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 1
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 60.2A^2
  • Surface Charge: 0
  • Tautomer Count: nothing
  • XLogP3: nothing

Experimental Properties

  • Color/Form: Viscous liquid
  • Density: 1.0313 (rough estimate)
  • Melting Point: 25°C
  • Boiling Point: bp0.2 175-179°
  • Flash Point: 226.6°C
  • Refractive Index: 1.5600 (estimate)
  • PSA: 60.17000
  • LogP: 3.55600
  • Solubility: Soluble in ether

Primaquine Security Information

Primaquine Customs Data

  • HS CODE：2933499090
  • Customs Data：

    China Customs Code:

    2933499090

    Overview:

    2933499090. Other compounds containing quinoline or isoquinoline ring system [but not further fused]. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:20.0%

    Declaration elements:

    Product Name, component content, use to, Please indicate the appearance of Urotropine, 6- caprolactam please indicate the appearance, Signing date

    Summary:

    2933499090. other compounds containing in the structure a quinoline or isoquinoline ring-system (whether or not hydrogenated), not further fused. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Primaquine Pricemore >>

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abcr
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N4-(6-Methoxyquinolin-8-yl)pentane-1,4-diamine (2 H3PO4); .
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abcr
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Primaquine Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Sodium hydroxide Solvents: Water ;  rt
Reference
Synthesis and antimalarial activity of trioxaquine derivatives
Dechy-Cabaret, Odile; Benoit-Vical, Francoise; Loup, Christophe; Robert, Anne; Gornitzka, Heinz; et al, Chemistry - A European Journal, 2004, 10(7), 1625-1636

Production Method 2

Reaction Conditions
1.1 Reagents: Sodium hydroxide Solvents: Water ;  pH 10
Reference
Liver-targeting of primaquine-(poly-γ-glutamic acid) and its degradation in rat hepatocytes
Tomiya, Noboru; Jardim, Juliette G.; Hou, Jennifer; Pastrana-Mena, Rebecca; Dinglasan, Rhoel R.; et al, Bioorganic & Medicinal Chemistry, 2013, 21(17), 5275-5281

Production Method 3

Reaction Conditions
1.1 Reagents: Sodium hydroxide Solvents: Water ;  2 h, rt
Reference
Antimalarial and anti-inflammatory activities of new chloroquine and primaquine hybrids: Targeting the blockade of malaria parasite transmission
Boechat, Nubia; Carvalho, Rita C. C.; Ferreira, Maria de Lourdes G.; Coutinho, Julia Penna; Sa, Paula M.; et al, Bioorganic & Medicinal Chemistry, 2020, 28(24),

Production Method 4

Reaction Conditions
1.1 Reagents: Triethylamine Solvents: Dichloromethane ;  rt
Reference
Primaquine homodimers as potential antiplasmodial and anticancer agents
Pavic, Kristina; Rubinic, Barbara; Rajic, Zrinka; Fontinha, Diana; Prudencio, Miguel; et al, Bioorganic & Medicinal Chemistry Letters, 2019, 29(19),

Production Method 5

Reaction Conditions
1.1 Reagents: Sodium hydroxide Solvents: Water ;  rt; 2 h, pH 10, rt
Reference
New pentasubstituted pyrrole hybrid atorvastatin-quinoline derivatives with antiplasmodial activity
Carvalho, Rita C. C.; Martins, Wagner A.; Silva, Tayara P.; Kaiser, Carlos R.; Bastos, Monica M.; et al, Bioorganic & Medicinal Chemistry Letters, 2016, 26(8), 1881-1884

Production Method 6

Reaction Conditions
1.1 Reagents: Sodium hydroxide Solvents: Water ;  heated
Reference
Synthesis, cytotoxicity and antimalarial activity of ferrocenyl amides of 4-aminoquinolines
N'Da, David D.; Breytenbach, Jaco C.; Smith, Peter J.; Lategan, Carmen, Arzneimittel Forschung, 2010, 60(10), 627-635

Production Method 7

Reaction Conditions
1.1 Reagents: Methanol Solvents: Dichloromethane ,  Water ;  rt
Reference
Direct Deamination of Primary Amines via Isodiazene Intermediates
Berger, Kathleen J. ; Driscoll, Julia L.; Yuan, Mingbin; Dherange, Balu D. ; Gutierrez, Osvaldo ; et al, Journal of the American Chemical Society, 2021, 143(42), 17366-17373

Production Method 8

Reaction Conditions
1.1 Reagents: Sodium hydroxide ;  1 h, rt
Reference
Synthesis, characterization, and cellular localization of a fluorescent probe of the antimalarial 8-aminoquinoline primaquine
McQueen, Adonis; Blake, Lynn D.; Azhari, Ala; Kemp, M. Trent; McGaha, Tommy W. Jr.; et al, Bioorganic & Medicinal Chemistry Letters, 2017, 27(20), 4597-4600

Production Method 9

Reaction Conditions
1.1 Reagents: Hydrazine hydrate (1:1) Solvents: Ethanol ;  72 h, reflux
Reference
Synthesis of primaquine glyco-conjugates as potential tissue schizontocidal antimalarial agents
Azad, Chandra S.; Saxena, Mridula; Siddiqui, Arif J.; Bhardwaj, Jyoti; Puri, Sunil K.; et al, Chemical Biology & Drug Design, 2017, 90(2), 254-261

Production Method 10

Reaction Conditions
1.1 Reagents: Sodium hydroxide Solvents: Water ;  pH 9 - 10
Reference
Design, synthesis and biological evaluation of novel primaquine-cinnamic acid conjugates of the amide and acylsemicarbazide type
Pavic, Kristina; Perkovic, Ivana; Gilja, Petra; Kozlina, Filip; Ester, Katja; et al, Molecules, 2016, 21(12), 1629/1-1629/25

Production Method 11

Reaction Conditions
Reference
Macromolecular prodrugs. XII. Primaquine conjugates: synthesis and preliminary antimalarial evaluation
Rajic, Zrinka; Kos, Gabrijela; Zorc, Branka; Singh, Prati Pal; Singh, Savita, Acta Pharmaceutica (Zagreb, 2009, 59(1), 107-115

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